NO801501L - Fremgangsmaate for fremstilling av 3-tiovinylcefalosporiner - Google Patents
Fremgangsmaate for fremstilling av 3-tiovinylcefalosporinerInfo
- Publication number
- NO801501L NO801501L NO801501A NO801501A NO801501L NO 801501 L NO801501 L NO 801501L NO 801501 A NO801501 A NO 801501A NO 801501 A NO801501 A NO 801501A NO 801501 L NO801501 L NO 801501L
- Authority
- NO
- Norway
- Prior art keywords
- group
- substituted
- denotes
- formula
- dioxo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 179
- 229930186147 Cephalosporin Natural products 0.000 title claims description 18
- 229940124587 cephalosporin Drugs 0.000 title claims description 18
- 150000001780 cephalosporins Chemical class 0.000 title claims description 17
- -1 L-2-amino-2-carboxyethyl Chemical group 0.000 claims abstract description 551
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 105
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 claims abstract description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 14
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 claims abstract description 8
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims abstract description 7
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims abstract description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 299
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 260
- 230000002829 reductive effect Effects 0.000 claims description 178
- 125000006239 protecting group Chemical group 0.000 claims description 74
- 239000002253 acid Substances 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 34
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000004442 acylamino group Chemical group 0.000 claims description 18
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 13
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000003573 thiols Chemical class 0.000 claims description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 10
- 125000004306 triazinyl group Chemical group 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 8
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- 150000007530 organic bases Chemical group 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 150000007970 thio esters Chemical class 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005354 acylalkyl group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 3
- 229960003151 mercaptamine Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 654
- 239000000243 solution Substances 0.000 description 314
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 272
- 239000000047 product Substances 0.000 description 247
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 202
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 168
- 239000011541 reaction mixture Substances 0.000 description 162
- 238000002329 infrared spectrum Methods 0.000 description 137
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 133
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 130
- 238000001228 spectrum Methods 0.000 description 129
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 124
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 116
- 239000000741 silica gel Substances 0.000 description 108
- 229910002027 silica gel Inorganic materials 0.000 description 108
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 101
- 239000007787 solid Substances 0.000 description 93
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 81
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 80
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 65
- 235000019253 formic acid Nutrition 0.000 description 65
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- 229910052938 sodium sulfate Inorganic materials 0.000 description 61
- 235000011152 sodium sulphate Nutrition 0.000 description 61
- 238000001914 filtration Methods 0.000 description 54
- 239000002904 solvent Substances 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000012153 distilled water Substances 0.000 description 42
- 239000000706 filtrate Substances 0.000 description 42
- 239000000843 powder Substances 0.000 description 42
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
- 238000003756 stirring Methods 0.000 description 35
- 238000001816 cooling Methods 0.000 description 33
- 238000010992 reflux Methods 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 32
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 32
- 235000017557 sodium bicarbonate Nutrition 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000126 substance Substances 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 24
- 238000001035 drying Methods 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- 239000011734 sodium Substances 0.000 description 22
- 229910052708 sodium Inorganic materials 0.000 description 22
- 239000000725 suspension Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 20
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 18
- 159000000000 sodium salts Chemical class 0.000 description 18
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000007792 addition Methods 0.000 description 15
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- 150000003462 sulfoxides Chemical class 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 244000309464 bull Species 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 6
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7913095A FR2474504A1 (fr) | 1979-05-23 | 1979-05-23 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| FR7927687A FR2469415A2 (fr) | 1979-05-23 | 1979-11-09 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| FR8000978A FR2474035A2 (fr) | 1979-05-23 | 1980-01-17 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| FR8003057A FR2475545A1 (fr) | 1980-02-12 | 1980-02-12 | Nouveaux thioloesters, leur preparation et leur utilisation en synthese |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801501L true NO801501L (no) | 1980-11-24 |
Family
ID=27446397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801501A NO801501L (no) | 1979-05-23 | 1980-05-21 | Fremgangsmaate for fremstilling av 3-tiovinylcefalosporiner |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4307116A (nl) |
| AU (1) | AU534807B2 (nl) |
| BE (1) | BE883415A (nl) |
| CA (1) | CA1145744A (nl) |
| CH (1) | CH645117A5 (nl) |
| DE (1) | DE3019400A1 (nl) |
| DK (1) | DK222180A (nl) |
| ES (1) | ES491686A0 (nl) |
| FI (1) | FI801640A (nl) |
| GB (1) | GB2051788B (nl) |
| GR (1) | GR68074B (nl) |
| HU (1) | HU184771B (nl) |
| IE (1) | IE50626B1 (nl) |
| IL (1) | IL60138A (nl) |
| IT (1) | IT1148830B (nl) |
| LU (1) | LU82479A1 (nl) |
| NL (1) | NL8003011A (nl) |
| NO (1) | NO801501L (nl) |
| NZ (1) | NZ193798A (nl) |
| PH (1) | PH15929A (nl) |
| PL (1) | PL125471B1 (nl) |
| PT (1) | PT71275A (nl) |
| SE (1) | SE8003820L (nl) |
| YU (1) | YU136780A (nl) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3165922D1 (en) * | 1980-03-28 | 1984-10-18 | Biochemie Gmbh | New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production |
| FR2494274A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| EP0071370A3 (en) * | 1981-07-23 | 1984-05-16 | Ici Pharma | Cephalosporin derivatives, process for their preparation and pharmaceutical compositions containing them |
| US4526977A (en) * | 1981-10-07 | 1985-07-02 | American Home Products Corporation | 2-(3-Amino-5-isoxazolyl)-2-oxyimino-acetic acids |
| FR2532315A1 (fr) * | 1982-08-27 | 1984-03-02 | Rhone Poulenc Sante | Formes cristallisees de sels d'addition avec des acides, de l'((amino-2-thiazolyl-4)-2 methoxyimino-2 acetamido)-7 carboxy-2 (dioxo-5,6 formylmethyl-4 tetrahydro-1,4,5,6 triazine-1,2,4 yl-3) thio-2 vinyl)-3 oxo-8 thia-5 aza-1 bicyclo(4.2.0) octene-2 isomere syn, forme e et leur preparation |
| GR79043B (nl) * | 1982-12-06 | 1984-10-02 | Fujisawa Pharmaceutical Co | |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
| JPS6064986A (ja) * | 1983-09-20 | 1985-04-13 | Toyama Chem Co Ltd | セファロスポリン類の製造法 |
| KR850001206B1 (ko) * | 1984-04-27 | 1985-08-20 | 한국과학기술원 | 세펨 유도체의 제조 방법 |
| IE58487B1 (en) * | 1984-09-07 | 1993-09-22 | Kaisha Maiji Seika | New cephalosporin compounds and the production thereof |
| US4645769A (en) * | 1985-03-01 | 1987-02-24 | Merck & Co., Inc. | 1-oxa-1-dethia-cephalosporin compounds and antibacterial agent comprising the same |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| US4699981A (en) * | 1985-08-12 | 1987-10-13 | Taisho Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| JPS62205088A (ja) * | 1986-03-03 | 1987-09-09 | Meiji Seika Kaisha Ltd | 新規セフエム化合物 |
| DE69331576T2 (de) * | 1992-09-18 | 2002-10-17 | Otsuka Kagaku K.K., Osaka | Cephem-verbindungen, verfarhren zu ihrer herstellung und diese enthaltende medikamente |
| MY127641A (en) * | 1995-10-12 | 2006-12-29 | Essential Therapeutics Inc | Cephalosporin antibiotics |
| US6025352A (en) * | 1997-09-29 | 2000-02-15 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| US6030965A (en) * | 1997-09-30 | 2000-02-29 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| US20050267092A1 (en) * | 2002-02-28 | 2005-12-01 | Chang-Seok Lee | Novel cephalosporin compounds and process for preparing the same |
| EP2209474A4 (en) | 2007-10-09 | 2013-07-24 | Sopharmia Inc | BROAD SPECTRUM BETA-LACTAMASE INHIBITORS |
| WO2014165126A2 (en) | 2013-03-12 | 2014-10-09 | Sopharmia, Inc. | Derivatized 3-styryl-cephalosporins |
| CN103224473B (zh) * | 2013-05-16 | 2015-04-15 | 黑龙江大学 | 一种三嗪环的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US3983113A (en) * | 1975-08-15 | 1976-09-28 | Syntex (U.S.A.) Inc. | Cephalosporin type antibacterials |
| US4202893A (en) * | 1976-03-25 | 1980-05-13 | Roussel Uclaf | Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids |
| US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
| JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
-
1980
- 1980-05-21 IT IT22240/80A patent/IT1148830B/it active
- 1980-05-21 LU LU82479A patent/LU82479A1/fr unknown
- 1980-05-21 ES ES491686A patent/ES491686A0/es active Granted
- 1980-05-21 PL PL1980224389A patent/PL125471B1/pl unknown
- 1980-05-21 AU AU58596/80A patent/AU534807B2/en not_active Ceased
- 1980-05-21 DK DK222180A patent/DK222180A/da not_active Application Discontinuation
- 1980-05-21 YU YU01367/80A patent/YU136780A/xx unknown
- 1980-05-21 CH CH398880A patent/CH645117A5/fr not_active IP Right Cessation
- 1980-05-21 GR GR62014A patent/GR68074B/el unknown
- 1980-05-21 NZ NZ193798A patent/NZ193798A/xx unknown
- 1980-05-21 GB GB8016728A patent/GB2051788B/en not_active Expired
- 1980-05-21 SE SE8003820A patent/SE8003820L/ not_active Application Discontinuation
- 1980-05-21 DE DE19803019400 patent/DE3019400A1/de not_active Withdrawn
- 1980-05-21 IE IE1061/80A patent/IE50626B1/en unknown
- 1980-05-21 PT PT71275A patent/PT71275A/pt unknown
- 1980-05-21 CA CA000352357A patent/CA1145744A/fr not_active Expired
- 1980-05-21 US US06/152,115 patent/US4307116A/en not_active Expired - Lifetime
- 1980-05-21 HU HU801277A patent/HU184771B/hu unknown
- 1980-05-21 FI FI801640A patent/FI801640A/fi not_active Application Discontinuation
- 1980-05-21 NO NO801501A patent/NO801501L/no unknown
- 1980-05-21 BE BE0/200706A patent/BE883415A/fr not_active IP Right Cessation
- 1980-05-22 PH PH24055A patent/PH15929A/en unknown
- 1980-05-22 IL IL60138A patent/IL60138A/xx unknown
- 1980-05-23 NL NL8003011A patent/NL8003011A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PH15929A (en) | 1983-04-27 |
| HU184771B (en) | 1984-10-29 |
| FI801640A (fi) | 1980-11-24 |
| SE8003820L (sv) | 1980-11-24 |
| BE883415A (fr) | 1980-11-21 |
| CH645117A5 (fr) | 1984-09-14 |
| IL60138A (en) | 1984-04-30 |
| YU136780A (en) | 1983-10-31 |
| US4307116A (en) | 1981-12-22 |
| PT71275A (fr) | 1980-06-01 |
| AU534807B2 (en) | 1984-02-16 |
| GB2051788B (en) | 1984-01-18 |
| NZ193798A (en) | 1983-11-18 |
| PL125471B1 (en) | 1983-05-31 |
| ES8102135A1 (es) | 1980-12-16 |
| LU82479A1 (fr) | 1980-12-16 |
| DE3019400A1 (de) | 1981-04-23 |
| ES491686A0 (es) | 1980-12-16 |
| NL8003011A (nl) | 1980-11-25 |
| GB2051788A (en) | 1981-01-21 |
| IE50626B1 (en) | 1986-05-28 |
| IT1148830B (it) | 1986-12-03 |
| IE801061L (en) | 1980-11-23 |
| GR68074B (nl) | 1981-10-30 |
| AU5859680A (en) | 1980-11-27 |
| PL224389A1 (nl) | 1981-02-13 |
| CA1145744A (fr) | 1983-05-03 |
| DK222180A (da) | 1980-11-24 |
| IT8022240A0 (it) | 1980-05-21 |
| IL60138A0 (en) | 1980-07-31 |
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